HCID 13288069, compound → HCID 13288070, compound

HRID 1903904Notes

Reaction equation

HRID 1903904 reaction equation
[CH:1]([NH:3][N:4]1[C:13]2[CH:12]=[C:11]3[O:14][CH2:15][O:16][C:10]3=[CH:9][C:8]=2[C:7](=[O:17])[C:6]([C:18]([O:20]CC)=[O:19])=[CH:5]1)=[O:2]>C(O)=O>[CH:1]([NH:3][N:4]1[C:13]2[CH:12]=[C:11]3[O:14][CH2:15][O:16][C:10]3=[CH:9][C:8]=2[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]1)=[O:2]

Participants

3

Reactant 1

HCID 13288069HCID 13288069, compound

Product 1

HCID 13288070HCID 13288070, compoundYield 43.7%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 5.8 g of ethyl 5-(formylamino)-5,8-dihydro-8-oxo-1,3-dioxolo[4,5-g]-quinoline-7-carboxylate (Example 3) and 100 ml of 97% formic acid was heated at reflux under a Dean-Stark separator for about eight hours. The reaction mixture was then distilled to remove 30 ml of volatiles, cooled and stirred to induce crystallization of product. The latter was collected by filtration and washed with absolute alcohol and ether to give 2.3 g of 5-(formylamino)-5,8-dihydro-8-oxo-1,3-dioxolo[4,5-g]quinoline-7-carboxylic acid, tan crystals, m.p. 302° C. (decompn.).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under a Dean-Stark separator for about eight hours
  3. distillationThe reaction mixture was then distilled
  4. customto remove 30 ml of volatiles
  5. temperaturecooled
  6. customcrystallization of product
  7. filtrationThe latter was collected by filtration
  8. washwashed with absolute alcohol and ether

Sources & evidence

ORD record
ord-46adf814d66542618218e1257b295af0
Source dataset
uspto-grants-1984_03
Patent number
US04439436

Reaction notes

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